Jail Diary

Readers of Reggie’s Jail Diary will encounter a surprising number of references to pills—sometimes by brand name, sometimes by abbreviations

Following the violation of his parole, Reg was sent to Sleepy Hollow Correctional Facility, where he would be held until

Reggie did not write on his first day in jail, so we pick up his story on Day 2. October

Morning again.  I slept well and despite my circumstances I awaken feeling well and content.  I had a good night’s

October 31 (Day 4) Again, I awaken feeling well rested, feeling good.  Today is Saturday and we are allowed to

November 1 (Day 5) I awoke this morning feeling shaken and uneasy due to a dream (nightmare?) I had during

November 2 (Day 6) I slept in this morning and had to run to the kitchen for breakfast.  I’m told

Today begins much like any other day in here.  I get up just in time to rush to the kitchen

November 4 (Day 8) Well … I’ve been here for a week and I’m still not sure if I’m having

November 5 (Day 9) Today is the ninth of my originally scheduled ten days here.  Hopefully, but not likely, it

November 6, 1998 Today, I went to court.  Before leaving I was strip searched (lest I try to smuggle something

November 7 (Day 11) Today is Saturday and I slept in till lunch.  I do enjoy this.  I was telling

November 8 (Day 12) Again, I sleep till 12:30, getting up just in time for lunch.  Today we eat like

November 9 (Day 13) The thirteen day of my thirteen days here.  Unlucky?  I think not.  It’s Monday, back to

November 10 (Day 14) Here I am, still in Sleepy Hollow.  Things are getting routine and it’s getting harder to

November 11 (Day 15) Finally, I get the writing paper I’ve been waiting for (they ran out yesterday).  Today’s a

November 13 (Day 17) Friday the 13th.  So far, so good.  I got up and won the game of Risk

November 15 (Day 19) Very quiet day today.  Spent most of the day playing Risk.  Frankie was supposed to come

November 16 (Day 20) It’s Monday again. Another week begins, and I hope this week brings something good, some progress.

November 20 (Day 24) Just another day here. They seem to be getting longer and longer. I gotta get outta

November 23 (Day 27) Today I’m preparing for my appearance in court. I’ve written some draft copies of a speech

I really fucking hope that this is my last day here. It’s not that things are that bad in here

Although Reg had violated the terms of his conditional sentence by taking drugs, and was now in jail, he was

In October 1998, Reggie MacDonald was several months into a conditional sentence for trafficking in cocaine. The sentence allowed him

Written ~ Nov. 28, 1998 Woe is me
Here I am
Confess your sins
Mortal man Been in treatment For so long
Never right
Oh

November 28 (Day 32) I’m feeling kinda bored today; having thought about moving down to medium. The time might go

December 3 (Day 37) I’m really getting sick of this place – feeling kind of alone and isolated today –

December 7 (Day 41) Never got any sleep again last night.  This has been going on for about a week

December 11 (Day 45) I left my pen downstairs and my lighter.  I just finished writing letters to Ann, Martin,

December 15 (Day 49) Today I got moved to medium.  I’m not sure if I like it here or not. 

December 20 (Day 54) It wasn’t a bad day today. I slept all morning and most of the afternoon. We

December 24 (Day 58) Christmas eve. This morning I got a letter from Santa Claus. I wrote to him as

December 26 (Day 59) I’m just glad the day is over. Today is my 60th day here (he was off

December 29 Another day down; two more left this year. I look forward to 1999 and hope it brings good

My brother wrote a fairy tale about a prison on a hill, four moats (one of them full of rubber

January 1, 1999 It is now 1999, 12:05 am and I must say that this is the worst new year’s

January 2-5, 1999 No journal entries. January 6 For 2 days and nights I laid on the floor of a

January 7, 1999 Not much to note for a week or so, this is probably because he did not have

These diary entries cover Reggie’s final two weeks in maximum security before his move to minimum. During this period he

January 21  My 90th day here and still I’m no closer to getting parole.  I’ve decided to change my strategy

January 25 It’s Johns last day here.  Tomorrow morning, he goes to court to be sentenced, likely to Springhill.  I

January 28 I’ll be glad when the weekend gets here.  Everyday seems to get a bit longer. Today I called

February 1 I moved to minimum today and I don’t like it here.  There’s a couple of guys here I

February 4 February 5 Forgot to write anything yesterday.  So bored I slept all day.  The days can be so

February 8 Fucked up the computer this morning.  Nothing too serious.  I deleted the File Manager icon, and nobody knows

February 13 Anne called today, from Ontario.  She’s not mad at me.  I’m surprised her call got through but I

February 15 This place is driving me foolish.  We got three more in here today, so there’s 15 now.  It’s

February 19 Got moved to medium this afternoon.  I’m back in the centre unit with John M., David W. and

February 24 Today I put in a request to talk to Verna about the book policy with an implied threat

February 26 Pills didn’t show up, but things went well today.  Paul M. from Summerside detox (good guy) came to

March 1 Hmmm … Well, John came down to medium [security] today.  We didn’t get him in our unit.  They

March 5 Each week I look forward more and more to the weekend.  Tonight we were able to stay up

March 7 The biggest news here today is that George Murphy was stabbed to death last night and Jody was

March 11 Today I got my own room which is a great relief as I hate sharing a room.  The

March 14 I slept all day today.  I didn’t get up (except for meals) till 5:00.  I hate Sundays so

March 17 This day went by quickly.  This morning I played with the typing tutor and got my speed up

March 23 Brian Smith showed up to talk to me today so he can get to work on the parole

March 25 Got a visit today from my mother and father which went alright.  No bad news.  I can’t think

March 27 I didn’t do much of anything today.  I wrote a letter to [my daughter].  Trying to make her

March 31 I didn’t make an entry yesterday because I was busy sleeping.  It was a dull day except for

April 3 I slept till five o’clock today so it was a short day and I’ve not much to say

April 6 Anger Management started again today.  I kinda enjoy this course.  Everybody talks about things that bug them and

April 7 Today I find myself back in max, via the hole.  Last night, most of our unit had decided

April 10 I’m really bored here.  I don’t like these guys I’m in with.  They are pinheads, especially the new

April 15 My mother’s birthday and she was in to visit today.  She’ll be back again Sunday with Steven and

April 20 Today I was able to get moved over to the other unit, with Tylers help.  The company is

April 25 And another weekend comes to its end.  Well it may be my last one here, I wonder.  Except

April 30 Things didn’t work out today; no word from Brian.  So, I’ll be in this fucking hole for another

May 1 Another dull day.  Another fucking month to go.  I guess it was pretty hot out today (25C) but

May 9 Tyler came back this evening, so all is back to normal.  They’re keeping Rueben for a while cause

May 11 I got a visit arranged today for Saturday with the kids.  I’m a-looking forward to that.  And I

May 14 An interesting day it was.  I was on the computer this afternoon and [Supervisor] called me to his

Reggie got bad news, in that his parole was denied.  As an outsider, looking in on the things that he

@ mid 1999 – Well, it’s almost noon.  I’m sitting here waiting for the guard to unlock my door, after

May 21 I was supposed to go to my first meeting as Unit Rep today, but they cancelled it.  Our

May 25 More bad news.  [xxx] now says he threw out my stuff.  I just lost 3 or 4 grand. 

June 13 The hole June 14 The hole June 15 Got back from the hole today.  I went in earlier

June 16 Today is [my son’s] birthday (all my kids are a year older since I came in here).  I

June 19 My toilet is being used to talk to Jody and the other girls in the female unit.  If

I assume this place was built with plans / goals of rehabilitating offenders but that goal seems to have gone

June 30 … it’s [my wife]’s birthday, but what does it matter?  I got moved to medium security yesterday.  So

July 4 Another weekend comes to an end.  John and I spent the past eight hours playing axis and allies. 

July 9 They came up with a new policy here where anybody coming in from outside or back from the

July 15 And each day brings me closer to freedom…. Very nice outside today.  I was out for three hours,

July 19 I haven’t been writing the past few days because my light has been out since Friday and I

July 30 This seemed like a long day.  I do want to get away from here for a while.  It’s

Prince County Addictions Treatment Facility In PEI, the legal system gives the offender many chances to reform themselves, and as

August 7 It was fairly boring around here today.  Luckily, I bought a lot of papers through the week and

to [the rehab facility] they smelled beer off me and that was it for my parole. I spent four hours

August 17 Just another boring day … Jim and I talked about opening a strip club when we get out.